Style Setter: Lily Kwong

In every interview, Lily Kwong—urban planner, landscape designer and artistic director—inevitably gets the same questions. “We talk about what I look like. What my fitness routine is. What I’m wearing,” she says, relaying a point of contention. “That seems to be a problem that a lot of women in my life are having.” In the wake of what she calls a “last straw interview,” the former-model-turned-environmentalist decided to do something better. She launched AskThemMore.com, a website and podcast where smart, creative women wouldn’t be bombarded with such inconsequential questions.

Guests, whom Kwong describes as “women who have taken non-traditional paths and live creatively,” come to her SoHo recording studio and talk for an hour. Since launching this summer, Kwong has interviewed poet Cleo Wade on the experience of growing up biracial in the South, and entrepreneur Kristy Caylor on how to know it’s time to change careers. With her very first guest, DJ Chelsea Leyland, they skipped the small talk about fashion choices and playlists to discuss Leyland’s little-known struggle with epilepsy. “Music is really important to who she is, but the struggle she has experienced fundamentally transformed her life,” says Kwong. “I wanted to give her a space to talk about it.”

AskThemMore.com came out of Kwong’s desire to not only provide an alternative to the shallow interview, but also glean inspiration and share that with others. High on her list of dream guests is one of her greatest inspirations, Oprah. “I used to rush home as a little girl for Oprah,” she says. “Watching her ask questions really made an impact.”